That Connection with You

Story Info
Roxy's kinky first time with her Asexual best friend.
5.4k words
4.58
2.8k
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Okay, I think it's time for a break."

Smooth brown hair met freshly washed pillow as Roxy fell back onto the bed, letting go of her controller as she did so. The fluffiness of the pillow and the light scent of lavender that emanated from the sheets made her feel cozy and at home - which was a wonderful feeling, given that it was neither her home, nor her bed.

"Yeah, we have been losing kind of badly these past few games."

Roxy felt the bed jostle slightly as another body fell beside hers. Despite her exceptional comfort, she adjusted slightly to face her companion. His lighter brown hair - just on the verge of blonde - covered his eyes as he pressed himself into the bed with his hands behind his head. The strands shuffled with the rhythmical tapping of his legs against the bed frame.

The thumping made Roxy aware of her own heartbeat, which had once been following that rhythm, but was now quickly moving into double time. Blood rushed to her cheeks as she stared wordlessly at her friend, gently scanning him from top to bottom.

"Rox? Everything okay?"

Roxy's head snapped up to meet her friend's now-visible eyes. His head was cocked slightly, with an adorably concerned pout that made her want to just roll over and squeeze him.

Don't, don't you do it. Just answer him. That's your out. Take the out.

"S-sorry Jesse, I'm just... a little frustrated. It was a lot of losses in a row."

"Yeah, sorry, I'm pretty rusty."

"No, no, it's not your fault! I'm not the best either. Sometimes, you just lose, right?"

Jesse nodded with a gentle smile. "Well, if we're taking a break, we should have snacks! I'll get some, and a few drinks, and then we can swap to something else!"

"That sounds good! Need any help?"

"No, no, you're my guest! I've got it. Why don't you look and see what you'd like to play next?"

"Oh, sure, I can do that."

With the plan set, Jesse heaved himself out of the bed, nearly tumbling over his long legs as he did so. Steadying himself, he waved a small goodbye to Roxy before walking out of the bedroom.

Once the sound of his footsteps faded, Roxy turned, pressed her face into the pillow, and let out a frustrated moan.

Why does he have to be so adorable in person, too!?

Flipping over to regain her breath, Roxy sat up and looked around the room. It wasn't a particularly large bedroom, but it was cozy and tidy. Across from the bed that she was sitting on was an entertainment center with a decently sized TV and a collection of gaming consoles. Beside that was a tower with countless games shelved inside of it. A small work desk rested against the wall near the door, upon which sat a computer, a few figurines, and the handbag that she had set down upon arrival. No tossed clothes, no loose trash - either Jesse was way more organized than even she was, or he had made sure to nicen up the room for her arrival. She wanted to give him the benefit of the doubt, but she couldn't help but feel like it was probably the latter. After all, this was their first-time meeting in person - no doubt he wanted to make a good first impression.

Not that he really needed to do that, since even just through their online interactions, Roxy had become smitten with him.

She couldn't even fully remember how long ago she had met her once-online-only friend. In college? Slightly before? It had been a few years since they'd graduated, so she knew that it had to have been a decent amount of time since they'd met one another. Even so, every time she looked at him, she felt less like an adult and more like an anxious teenager talking to her longtime crush. It was a miracle that he hadn't noticed why she had been playing poorly: she'd been staring at him with sparkles in her eyes instead of focusing on the screen. She desperately wanted to just tell him, to let the butterflies out of her chest, but she couldn't. It wouldn't mean anything.

After all, he wasn't into... well, anyone, as far as she knew.

For as long as she'd been talking to him, his asexuality had been a known quantity. It wasn't a secret - in fact, she'd found out fairly early on by pure chance, and nobody batted an eye about it. He was a sweetheart, one of the nicest people she'd ever known, and one of the few people she'd always enjoyed spending time with. But the thought that he wouldn't reciprocate - wouldn't be able to reciprocate - made her too hesitant to try.

Especially since if she knew that he felt similarly, she'd had shoved him into the bed and been riding him like a cowgirl already.

A light shock shot through her lower body as the thought popped into her head. A low, breathy moan escaped her lips as her body shuddered.

God damnit, why did I have to think about ittttt?

Roxy popped off the bed and started walking. Rather than heading over to the game tower to pick a game, however, she instead made her way over to her bag, which sat on Jesse's desk.

Gum, a mint, something I can put in my mouth - she flicked herself, knowing what she really wanted to have there - I've gotta have something I can...

"Shit," she whispered as she stopped thumbing through the contents of her bag.

"Everything okay?"

"AAH!"

Roxy stumbled back as Jesse reentered the room with a couple of bowls of snacks. Her bag tumbled out of her hands, spilling its contents across the bedroom floor. She stared at the dispersed items for a moment before whipping her hazel eyes over to Jesse. She felt like her face couldn't have gotten any redder, until she realized that he wasn't looking at her. The heat in her cheeks rose as her eyes followed his line of vision back to the object of his focus.

The reason she'd cursed in the first place.

The thing she hadn't meant to bring.

The one thing she didn't want him to see.

Nestled neatly on top of the pile, like a little kinky treasure, was a black leather collar with a wrapped-up leash.

Frozen silence drifted around the room. Both parties remained deathly still for a moment.

A minute.

One thousand years.

The Earth could have imploded and the two of them wouldn't have noticed a thing.

Finally, as if the switch on time had flipped from "Incomparably slow" to "I'm Barry Allen," Roxy reached out, grabbed the collar, and slammed it back into the bag.

"Y-you didn't s-s-see that," she stuttered, incapable of even looking directly at Jesse. She reached out to grab more of her bag's contents but was just as quickly stopped by the man gently placing his hand on hers. She looked up at him, flush with a mixture of embarrassment and lust, tears forming at the edges of her eyes. He looked back at her with a gentle, understanding smile, though even he couldn't hide his own light blush.

"It's okay, it's okay. No judging. You like what you like, right?"

Roxy dropped the bag and the items she'd been shoveling into it. She stared at him, stared through him. Longingly, intently. She stared into his eyes, at the redness of his cheeks, at the lips that were so, so close to her own. Her eyes stayed locked there, unable to pull away, unable to move even the slightest bit closer.

Jesse watched as her eyes darted around, then settled. He looked down towards his lips, then back up to her.

"Is... is everything okay?"

"I... I don't... I want..." she couldn't lie to him, but the words just wouldn't come out right. Alarms fired in her head. Conflicting thoughts flooded her brain en masse, leaving her incapable of getting a single answer out.

Go for it.

Don't go for it.

He already knows.

He's okay with it.

He just says he's okay with it.

We've known each other for so long.

We just met-

"Mmmf!"

The storm of thoughts was blown away as Jesse leaned in, placed a hand on her cheek, and brought his lips to hers. It was a gentle, loving kiss, one that made Roxy and her hesitation melt into his embrace. She watched him as his lips slowly drifted away from hers, cheeks a perfect rose and eyes glistening like the sun against the sea. For a moment, they stared at each other, lips still slightly parted with shallow breaths. Then, a single thought filled the space in Roxy's mind that the kiss had cleared away.

Go get him, girl.

"Rox-whoa!"

Jesse fell back against the floor as Roxy pounced on him, planting her lips against him again as she took him to the floor. Unlike the previous, gentle kiss, this one was full of passion. To Roxy's delight, Jesse immediately reciprocated, holding her as she returned his kiss with enthusiasm.

Roxy held the kiss for a few more moments before she realized what she had done and pulled herself away. Jesse cocked his head to the side as she sat back against his legs.

"Oh-oh god, I'm so sorry, I didn't mean- I mean I did, it's totally what I wanted and what I've been wanting but I didn't want to- I mean I totally did and I want more but I shouldn't have but then you did and you- and I- words!"

With a frustrated sign, Roxy buried her face in her hands. She couldn't believe that she'd just done what she'd done, even if Jesse had technically instigated it. Embarrassment was nothing new to the woman, but this was an entirely new level. And the worst part of it was, despite all of that frustration and surprise and embarrassment, she was completely and utterly soaked. Any more drenched and she would have sworn that she'd orgasmed from the kiss alone. She peeked through her fingers at Jesse, just enough to catch the slightest hint of a smile on his face. Curious, her hands slid down just enough to give her a full few of the man's bright grin.

"You're the cutest, you know that, Roxy?"

"Sh-shut up!" She smacked his arm in embarrassment, causing him to chuckle. "W-why did you..."

"Why did I kiss you?"

"Yes! Aren't you... you know..."

"Asexual?"

Roxy nodded sheepishly.

"Yes, I'm asexual. Not aromantic," he laughed. "I still feel that connection, silly. And..." he looked away slightly, "...and I feel that connection with you."

"...damnit, come back here!"

Grabbing his shirt, Roxy pulled Jesse back up into another kiss and held him there. Wrapping his arms around her, Jesse returned the kiss, and then the next, and the next. Each kiss between them slowly became deeper, more intimate, more fulfilling as they sat in each other's embrace. And with each lock of their lips, Roxy felt herself wanting more. Her pent-up frustration gradually turned to raging lust as she kept him locked in place. Eventually, kisses just weren't enough to sate it.

After one final, deep embrace, Roxy gently pushed Jesse away. He stared at her in awe as they both panted to catch their breath.

Now or never.

"Hey, Jess?" Roxy swallowed.

"Y-yeah?"

"How, uh... how comfortable are you with... you know... sex?"

"I, uh... I don't have very much experience, given, you know..."

"R-right..."

"But... I'd be willing to try. If you want."

"Are you sure?"

Jesse nodded. "I'd like to, with you. If, you know, you want to..."

I'm going to wreck this man, Roxy thought before shaking her head. No, no, that'll come later.

Roxy leaned back against her partner and smiled, with just a little hint of devilishness in her eyes. "Don't worry," she assured him as she ran her hand along his chest, "I can take the lead."

Removing herself from her partner's lap, Roxy helped Jesse to his feet. They finished gathering up Roxy's belongings and placed the bag back on the desk, next to the snack bowls that Jesse had apparently placed down before they'd exchanged kisses. With their hands now free, they slowly began to remove each other's clothing, starting with Roxy's. The blushing woman guided Jesse with every piece that fell to the ground; moving his hands across her body, she let him feel everything. Her shoulders, her breasts, her sides and her hips, her stomach, her legs - until finally, she brought his hands to her glistening pussy. She pressed his two of his fingers against her clit, slid them down, and led them inside of her, guiding him to her most sensitive spots and letting him experience her reactions.

After a bit, Jesse's hands began to move by himself, running fingers along her body and playing with the spots to which she had guided him. His heart leapt as she cooed and moaned and gasped at his touch, enraptured by the gentle force pressing every button, every sensory spot. Self-care couldn't compare to what she was experiencing as he explored her body inside and out. She felt his care for her, his wish to pleasure her, his submission to her guidance. It was bringing every desire out of her at once.

Having started him along, she began to remove his clothes as well, tracing his chest, the muscles on his arms, his sides, his thighs, until he, too, was letting out light grunts and moans. She teased his body before approaching his boxers, taking in his moans and shudders while he pleasured her in turn. His stated lack of experience was written all over his face as he panted and struggled against the new sensations he was both feeling and providing. As she watched his expression shift under her control, an idea crept into her head.

"Mmm, hey, you want to try one more thing before we start?"

"I - ah! - I guess? What did you haaave in mind?"

"I'll show you in a second. Go sit on the bed for me?"

"Um, okay?"

With only a twinge of hesitation, Jesse turned and walked to his bed. Taking a seat at the edge, he watched as Roxy walked over to the desk and reached her hand into the bag. Even with the lingering physical sensations running through his head, he immediately knew what she was getting: the collar that had spilled from her bag earlier.

Sure enough, Roxy turned back with the collar wrapped around the fingers of her left hand. Her right hand was slowly unravelling the leash. A mischievous grin spread across her face.

"You know, I really didn't mean to bring this. Normally it's, uh, just for me," she blushed. "Buuut..." she walked up to the bed and leaned in close to Jesse's face. "I think you'll look a lot cuter in it. Willing to give it a try?"

Jesse blinked at her, and then at the collar, as a strange shock shot through his chest. He wasn't a stranger to kink play in the form of media, but he'd never really done any himself. So even he was surprised at how excited he was getting at the thought of wearing it.

"...yes, please..." he finally managed to squeak out. Roxy's smile doubled at his response. Not a "sure," not an "okay," but a "yes, please?" She was going to have so much fun with him.

Invigorated by his willingness to play, Roxy sashayed over to the bed, swinging her hips with delight as she closed in on Jesse. The man couldn't take his eyes off of her as she leaned just barely over him and kissed him on the forehead.

"Ready?"

Jesse nodded, his eyes still fixated on her seductive smile.

"Then hold still."

With expert speed, she wrapped the collar snugly - but comfortably - around her partner's neck. He put a hand up to the leather and rubbed it curiously before being gently pulled forward by the leash, landing just above Roxy's chest. She stared down at him with hearts in her eyes, watching him squirm ever so slightly in shock. Backing off, she placed a finger to his lips until he settled. Then, she leaned into his ear and whispered, "Don't worry, I'll be slow and gentle."

As she leaned back, Roxy pressed two fingers to Jesse's chest and pushed him until he was lying on the bed, legs hanging over the edge.

"Now then, let's get you nice and- oh!" Roxy gasped a bit as she traced her fingers down Jesse's chest and landed on his dick. She had been prepared to give him some heavier stimulation to get him hard, but he was already bulging through his boxers. Someone must be liking that collar more than I thought, she smiled. I'll have to get him his own... While she mentally shopped for a collar that she thought might suit her new lover, her hands were slowly working his boxers off. Eventually, she lifted them off of him, revealing his smooth, still hardening dick.

"Mmm, hey Jesse?"

"Y-yeah?"

"Nice cock."

"S-shut up!" Jesse covered his face to both hide his blush and stifle his laughter. While he wasn't looking, Roxy began to run her fingers along his shaft. Small moans escaped from behind his hands as she gently stroked him. And single finger became two, became three, and soon she had her hand held gently around his throbbing cock. Precum trickled down his length as Roxy teased him and pulled on his collar, taking her time to draw out as many delicious sounds as she could from her man. After some light teasing, he was slick enough for her to begin lightly stroking. She moved her hand slowly, holding just firm enough to feel him twitch and pulse in her grip. After a while, his moans were joined by grunts and heavy breaths, all of which served to turn Roxy on even further. Without thinking, her other hand drifted down to her clit. She rubbed herself gently as she toyed with Jesse, allowing her own moans to mix with his.

After a few more minutes of teasing, Roxy gradually relaxed the hand on Jesse's dick, allowing him to relax and fall fully into the bed. His scarlet cheeks rose with each relieved pant, and the hands that had been gripping his sheets relaxed and released their hold.

"Are you alright?"

"Y-yeah... it's so different having someone else do it, though..."

"Better, right?" she smiled.

"Much," he smiled back.

"Mind if I come up there and make it feel amazing?"

"Yes please."

"Good boy."

Jesse's heart fluttered as the words left her lips and she began to crawl onto the bed. She guided him into rotating so that he was laying longways on the bed before she straddled him. Her dripping pussy hovered over his fully erect and twitching cock. Slowly, she lowered herself down onto its head. Soaked as she was, she knew that she could have just put the whole thing inside of her at once. But looking at Jesse's tense, pleasured expression and hearing him grunt and moan at the sensation of entering her, she couldn't help but want to tease him just a little bit longer. Being careful not to drop her weight too much, she began lightly bouncing on the tip of his cock, teasing his head with slow, controlled thrusts.

The focused stimulation started to drive Jesse wild. He moaned and whimpered, just barely keeping himself from thrashing around with Roxy on top of him as she eased herself further and further onto his cock with each roll of her hips. Each time she lifted herself up, she pulled on the leash, forcing him to focus on her rhythm. As she got lower and lower, his grunts and whimpers began to overtake his moans, and his hands began grasping the sheets with each pull of the leash. Seeing him struggle, Roxy leaned over, gently grabbed his wrists, and pinned them to the bed. Jesse stared at her, his heavy breaths keeping him from asking her what she was doing.

"You don't get to move around unless I tell you to, got it?"

Jesse nodded weakly; his head was too hazy from the near-torturous pleasure she had been inflicting on him to verbalize a response.

"Good. Now be a good boy and enjoy this~"

Pushing his arms as she went, Roxy leaned forward and pressed her tits into Jesse's face. His muffled sounds of surprise quickly turned into more moans as she began to ride him more quickly. It took everything out of Roxy to not just start slamming her hips down on him instead of pacing herself, but the sounds and vibrations of his moans wrapping around her body through her chest made it too enjoyable to stop.

Every few thrusts, Roxy would lean back to give Jesse a chance to breathe, using the leash to pull him up with her each time. Each tug caused his dick to twitch inside of her, sending shivers of pleasure up her spine that left her aching for more. His voice began to grow slightly strained from the grunts of pleasure and the uneven breaths, as each time Roxy fell back onto him, she pinned him and smothered him once more.

12